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Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's "Achilles Heel"

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Fürstner,  A.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Aïssa,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Chevrier,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Teplý,  F.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Nevado,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Tremblay,  M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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z601859_s.pdf
(Supplementary material), 73KB

Citation

Fürstner, A., Aïssa, C., Chevrier, C., Teplý, F., Nevado, C., & Tremblay, M. (2006). Studies on Iejimalide B: Preparation of the Seco Acid and Identification of the Molecule's "Achilles Heel". Angewandte Chemie International Edition, 45(35), 5832-5837. doi:10.1002/anie.200601859.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0025-AD46-8
Abstract
Limitations of models in total synthesis are illustrated by a study towards the potent cytotoxic macrolide iejimalide B. Although the Yamaguchi protocol allowed for the esterification of elaborate segments, attempted macrolactonization of the seco acid met with failure (see scheme, Boc= tert-butyloxycarbonyl). The assembly of the seco acid involves some of the most advanced applications of the Julia olefination known to date.